Water → N-[2-(4-Carboxyphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

HRID 580618Notes

Reaction equation

HRID 580618 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][OH:13])[CH:6]=1)[CH2:3][NH2:4].[C:14]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](=O)[CH3:32])=[CH:26][CH:25]=1)([O:16]CC1C=CC=CC=1)=[O:15].O>C1(C)C(C)=CC=CC=1>[C:14]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][OH:13])[CH:6]=2)[CH3:32])=[CH:26][CH:25]=1)([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 129448344-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenolHCID 201342441-(4-Carbobenzyloxyphenyl)propan-2-one

Product 1

HCID 19910572N-[2-(4-Carboxyphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine (1.09 g) and 1-(4-carbobenzyloxyphenyl)propan-2-one (1.6 g) were refluxed in xylene in a Dean and Stark apparatus until the theoretical amount of water had been collected. The solvent was removed, ethanol added and the mixture hydrogenated at 70 psi and 50° for 3 hours using 10% Pd/c as catalyst. Filtration of the catalyst and evaporation of the solvent gave the title compound as a foam τ (d6DMSO) 8.95 (3H, d, J=7 Hz), 6.8-7.4 (5H, m), 5.5 (2H, s+1H, t), 3.65 (5H, broad), 2.3-3.3 (5H, m), 2.0 (2H, d, J=8 Hz).

Workup

  1. customhad been collected
  2. customThe solvent was removed
  3. additionethanol added
  4. filtrationFiltration of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-14e2f9be7ba64461b7141233ca33dcfa
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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